Alphabet Boys

iHeartPodcasts and Western Sound

29 episodes listed below

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Secret cases, public consequences.

The gist

Alphabet Boys follows federal law enforcement into the hidden rooms where informants, agents, and targets shape criminal cases. Its strongest episodes turn secret recordings and court records into a wider argument about power, pressure, and accountability.

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About Alphabet Boys

Alphabet Boys is a measured investigative series about federal undercover work and the stories built around it. Trevor Aronson reports from the space where policing, politics, informants, and ambition overlap. The show does not treat secret operations as inherently heroic. It asks what happens when the government helps create the conditions for the crime it later prosecutes. One season follows Mickey Windecker, an FBI informant who infiltrated a racial justice protest scene in 2020. The reporting keeps returning to Zeb Hall, an activist left carrying the legal consequences of a case shaped by federal money, pressure, and surveillance. That human cost gives the series its force. Another season widens the lens into an international weapons deal involving Flavio Giorgescu, Massimo Romagnoli, Christian Ventilla, informants, agents, and a deal staged across Europe. The facts are complicated, but the show does not hide behind complexity. It lays out phone calls, testimony, undercover recordings, and evasions, then asks who benefited from the official version. The pacing is deliberate. Scenes do real work. A motorway, a hotel lobby, a LinkedIn entry, a sentencing call, or a stubborn refusal to be interviewed can carry as much weight as a legal argument. The show also uses update episodes and related reporting to connect its investigations to lawsuits, court petitions, extremism, mass violence, and federal counterterrorism strategy. Those connections are not decorative. They show a recurring concern with institutions that protect their own narratives. Alphabet Boys suits listeners who can sit with ambiguity but still want a reporter willing to draw conclusions. It is skeptical without becoming glib. It can be dryly funny, especially when official language begins to collapse under its own absurdity. But the center is serious: people lose freedom, reputation, safety, and trust while agencies defend the operation. That makes the show less a parade of cases than a continuing argument about what public safety is supposed to mean.

Made for: For listeners drawn to investigative true crime, federal law enforcement, informants, protest policing, and the gray areas inside undercover operations. Best suited to people who want documents, recordings, and patient argument over sensational retelling.

What sets it apart: Alphabet Boys stands apart by making the undercover process itself the subject. It follows the incentives and paper trail behind federal cases, then keeps asking whether the operation exposed danger or manufactured it.

In their own words

Alphabet Boys reveals the secret investigations of the FBI, DEA, ATF, and other alphabet agencies. Hosted by journalist Trevor Aaronson, Alphabet Boys exposes secret undercover recordings that the government never wanted the public to hear. We explore cases that are both dangerous and absurd in order to ask this question: Are America’s top cops catching criminals -- or creating them? Season two is “Up In Arms.” An international weapons deal to arm rebels in Colombia tangles up the DEA, the CIA, and the FBI in the same case. But who’s the good guy? And who’s the bad guy? This...

As heard by us

Based on 6 episodes we listened to · September 2026

Alphabet Boys turns undercover recordings and contested testimony into a precise examination of how federal stings produce evidence, leverage, and doubt.

Alphabet Boys follows federal investigations from inside the machinery, where informants, undercover agents, targets, and competing agencies can make guilt difficult to read cleanly.

Read our full review in PlayNext →

Why you'd press play

A botched arms sting turns the alphabet agencies into your least reassuring group chat.

Press play if you want

  • Trevor Aaronson to follow the undercover recording past the government's clean version
  • the point where informants, agents, and targets stop fitting into tidy moral boxes
Read the full recommendation in PlayNext →
FBI informantsundercover recordingsfederal sting operationsracial justice protestsinternational weapons dealscourt testimonycounterterrorism strategyofficial narratives

Talks about

Best episodes of Alphabet Boys

Short reviews from the PlayNext desk, based on the episodes we processed.

Introducing: Into the Madness, new from Trevor AaronsonFeb 20, 2025

A grim, reporting-driven setup that turns a mass shooting into a study of conspiracy and extremism.

Trevor Aronson opens a seven-part investigation into the 2022 mass shooting in Highland Park, Illinois, and keeps the focus from narrowing too quickly on the attack alone.

Introducing Pulse: The Untold StoryJul 11, 2024

An eight episode investigation of Pulse and the FBI history around the case.

Pulse: The Untold Story follows Trevor Aronson's eight episode look at the Pulse nightclub shooting, and it keeps coming back to the hidden relationship between the FBI, the shooter, and his father.

10. See Something, Say NothingJul 27, 2023

A skeptical, document-led look at how stings and self-mythology become public truth.

Alphabet Boys moves from a flattering National Geographic portrait of the DEA into the mechanics around Manzo Al-Kassar, then into the later self-reinventions of Massimo and Christian Ventilla. It is strongest when it treats those public remakings as evidence, not decoration.

9. Tomorrow I'm Going to Rob the BankJul 24, 2023

A Montenegro arrest story where help, cover, and loyalty stay in tension.

Set in Montenegro, this episode follows Flavio's cooperation with the DEA, Massimo Romagnoli's version of the trip, and the lingering question of whether the CIA call was help, cover, or both.

8. Welcome to the Sh*tshowJul 20, 2023

A DEA sting in Montenegro becomes a study in aliases, pressure, and institutional mess.

This episode follows a DEA sting in Montenegro as Juan, operating as Alex Diaz, moves through a waterfront hotel meeting with Flavio, Christian, Massimo, Diego, and Jorge.

8. The SpringsMar 21, 2023

A tense account of a Colorado Springs protest that turns a reflexive bike toss into a punishable moment.

The episode tracks a Colorado Springs protest crackdown with a steady, unsentimental eye, using police body-cam and witness accounts to show how quickly a demonstration slid into arrests.

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Episodes

  1. 1

    Introducing: DISGRACELAND

    Jul 9, 2026·2m
  2. 2

    Introducing: The Brothers Ortiz

    Dec 13, 2025·1m
  3. 3

    Introducing - The Burden: Get the Money and Run

    This episode is a promotional trailer for The Burden, a new true crime podcast introduced by Ben Adair, co-creator of Alphabet Boys.

    May 13, 2025·4m
  4. 4

    Introducing: Into the Madness, new from Trevor Aaronson

    This episode is the first chapter of Into the Madness, an Audible original series by Trevor Aronson investigating the 2022 Highland Park, Illinois Fourth of July parade shooting that killed seven people.

    Feb 20, 2025·38m·3 clips
  5. 5

    Introducing Pulse: The Untold Story

    Journalist Trevor Aronson introduces Pulse, The Untold Story, an eight-episode Audible investigation into the 2016 Pulse nightclub shooting in Orlando that killed 49 people.

    Jul 11, 2024·39m·3 clips
  6. 6

    Alphabet Boys, One Year Later

    One year after the first season of Alphabet Boys aired, host Trevor Aronson provides a brief update on the show's real-world impact.

    Feb 13, 2024·3m
  7. 7

    10. See Something, Say Nothing

    Hidden gem

    The episode starts by asking how official stories get built.

    Jul 27, 2023·37m·2 clips
  8. 8

    9. Tomorrow I'm Going to Rob the Bank

    Hidden gem

    Flavio Giorgetto is arrested in Montenegro.

    Jul 24, 2023·36m·2 clips
  9. 9

    8. Welcome to the Sh*tshow

    Hidden gem

    Juan arrives in Tivat for a DEA meeting.

    Jul 20, 2023·33m·2 clips
  10. 10

    7. Let's Make This Happen, Bro

    Jul 17, 2023·32m
  11. 11

    6. The Ramp Rat

    Jul 13, 2023·36m
  12. 12

    5. You Guys Are Not Serious

    Jul 10, 2023·30m
  13. 13

    4. Something We Might Look Into

    Jul 6, 2023·34m
  14. 14

    3. Codename Cardmember

    Jul 3, 2023·33m
  15. 15

    2. The Calls

    Jun 29, 2023·33m
  16. 16

    1. I Work for the CIA

    Jun 26, 2023·36m
  17. 17

    Introducing: Alphabet Boys: Season 2, Up in Arms

    Jun 20, 2023·3m
  18. 18

    Introducing Lost Hills: The Dark Prince

    Jun 12, 2023·11m
  19. 19

    10. America Didn't Send Its Best

    Apr 4, 2023·40m
  20. 20

    9. I Ain't A Snitch

    Mar 28, 2023·31m
  21. 21

    8. The Springs

    Episode 8 of Alphabet Boys follows the FBI's infiltration of left-wing activists in Colorado Springs, running parallel to the better-known Denver investigation.

    Mar 21, 2023·34m·3 clips
  22. 22

    7. They Call Me Juice

    Mar 14, 2023·31m
  23. 23

    6. Dumpster Fire

    Mar 7, 2023·30m
  24. 24

    5. Give 'Em Hell

    Feb 28, 2023·32m
  25. 25

    4. The Punisher

    Feb 21, 2023·39m
  26. 26

    3. Black Identity Extremism

    Feb 14, 2023·32m
  27. 27

    1. Summer of Rage

    Feb 7, 2023·33m
  28. 28

    2. All the Way Uptown

    Feb 7, 2023·34m
  29. 29

    Introducing: Alphabet Boys: Season One, Trojan Hearse

    Jan 30, 2023·3m